DE2311277A1 - Verfahren zur herstellung von perfluoralkylestern - Google Patents
Verfahren zur herstellung von perfluoralkylesternInfo
- Publication number
- DE2311277A1 DE2311277A1 DE19732311277 DE2311277A DE2311277A1 DE 2311277 A1 DE2311277 A1 DE 2311277A1 DE 19732311277 DE19732311277 DE 19732311277 DE 2311277 A DE2311277 A DE 2311277A DE 2311277 A1 DE2311277 A1 DE 2311277A1
- Authority
- DE
- Germany
- Prior art keywords
- integer
- acid
- formula
- reaction
- oleum
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 45
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 19
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 15
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 12
- 150000001735 carboxylic acids Chemical class 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 150000004694 iodide salts Chemical class 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 239000001530 fumaric acid Substances 0.000 claims description 6
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 6
- 239000004135 Bone phosphate Substances 0.000 claims description 5
- 239000003849 aromatic solvent Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- PSZAEHPBBUYICS-UHFFFAOYSA-N 2-methylidenepropanedioic acid Chemical compound OC(=O)C(=C)C(O)=O PSZAEHPBBUYICS-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 claims description 4
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
- -1 perfluoroalkyl iodides Chemical class 0.000 claims description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
- 239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 229940091181 aconitic acid Drugs 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 claims description 2
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims description 2
- 229940018557 citraconic acid Drugs 0.000 claims description 2
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 claims description 2
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 claims description 2
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 18
- 229910052740 iodine Inorganic materials 0.000 description 18
- 239000011630 iodine Substances 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
- D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH394072A CH565736A5 (enrdf_load_stackoverflow) | 1972-03-16 | 1972-03-16 | |
| CH1865972A CH575370A5 (enrdf_load_stackoverflow) | 1972-03-16 | 1972-12-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2311277A1 true DE2311277A1 (de) | 1973-09-27 |
Family
ID=25694235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732311277 Pending DE2311277A1 (de) | 1972-03-16 | 1973-03-07 | Verfahren zur herstellung von perfluoralkylestern |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3916009A (enrdf_load_stackoverflow) |
| JP (1) | JPS4911818A (enrdf_load_stackoverflow) |
| BE (1) | BE796813A (enrdf_load_stackoverflow) |
| CH (2) | CH565736A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2311277A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2175827B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1394947A (enrdf_load_stackoverflow) |
| IT (1) | IT979837B (enrdf_load_stackoverflow) |
| SU (1) | SU474970A3 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0103274A3 (de) * | 1982-09-11 | 1984-09-12 | Hoechst Aktiengesellschaft | Perfluoralkyl-malein- und -fumarsäureamide, Verfahren zu deren Herstellung und ihre Verwendung als schmutzabweisendes Mittel |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS51121985A (en) * | 1975-04-16 | 1976-10-25 | Iwasaki Electric Co Ltd | High pressure sodium lamp |
| US4029585A (en) * | 1975-07-26 | 1977-06-14 | E. I. Du Pont De Nemours And Company | Aqueous dispersions of perfluoroalkyl esters for treating textiles |
| JPS5485775U (enrdf_load_stackoverflow) * | 1977-11-29 | 1979-06-18 | ||
| WO1995011877A1 (fr) * | 1993-10-27 | 1995-05-04 | Elf Atochem S.A. | Alcools polyfluores et leurs procedes de preparation |
| US5814944A (en) * | 1996-01-22 | 1998-09-29 | Matsushita Electric Works, Ltd. | High pressure sodium vapor lamp with high color rendering |
| WO2002062735A1 (fr) * | 2001-02-07 | 2002-08-15 | Daikin Industries, Ltd. | Procede de preparation d'un melange de telomeres de iodure de fluoroalkyle et procede de preparation d'un ester de (meth)acrylate contenant du fluor |
| JPWO2005102982A1 (ja) * | 2004-04-26 | 2008-03-13 | ダイキン工業株式会社 | 含フッ素（メタ）アクリル酸エステルの製造方法 |
| JP4674604B2 (ja) * | 2006-03-10 | 2011-04-20 | ユニマテック株式会社 | ポリフルオロアルキルアルコールまたはその（メタ）アクリル酸誘導体およびそれらの製造法 |
| JP5493860B2 (ja) * | 2007-09-10 | 2014-05-14 | ユニマテック株式会社 | 含フッ素重合体およびこれを有効成分とする表面改質剤 |
| US8058463B2 (en) | 2007-12-04 | 2011-11-15 | E. I. Du Pont De Nemours And Compnay | Fluorosilanes |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3283012A (en) * | 1962-05-29 | 1966-11-01 | Du Pont | Process for preparing 2-perfluoroalkylethanol |
| FR1491513A (fr) * | 1966-06-30 | 1967-08-11 | Melle Usines Sa | Perfectionnements aux procédés de production d'esters et d'alcools |
| US3781370A (en) * | 1967-04-25 | 1973-12-25 | Allied Chem | Novel fluorinated alcohols |
| US3562310A (en) * | 1967-08-11 | 1971-02-09 | Allied Chem | Novel polysulfates and methods for their preparation |
| ZA714954B (en) * | 1970-09-03 | 1972-04-26 | Gen Electric | Thermosetting epoxy resins |
-
1972
- 1972-03-16 CH CH394072A patent/CH565736A5/xx not_active IP Right Cessation
- 1972-12-21 CH CH1865972A patent/CH575370A5/xx not_active IP Right Cessation
-
1973
- 1973-03-01 US US337028A patent/US3916009A/en not_active Expired - Lifetime
- 1973-03-07 DE DE19732311277 patent/DE2311277A1/de active Pending
- 1973-03-08 FR FR7308408A patent/FR2175827B1/fr not_active Expired
- 1973-03-09 GB GB1162573A patent/GB1394947A/en not_active Expired
- 1973-03-14 IT IT48792/73A patent/IT979837B/it active
- 1973-03-14 SU SU1894269A patent/SU474970A3/ru active
- 1973-03-15 BE BE128822A patent/BE796813A/xx unknown
- 1973-03-15 JP JP48029536A patent/JPS4911818A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0103274A3 (de) * | 1982-09-11 | 1984-09-12 | Hoechst Aktiengesellschaft | Perfluoralkyl-malein- und -fumarsäureamide, Verfahren zu deren Herstellung und ihre Verwendung als schmutzabweisendes Mittel |
Also Published As
| Publication number | Publication date |
|---|---|
| BE796813A (fr) | 1973-09-17 |
| CH565736A5 (enrdf_load_stackoverflow) | 1975-08-29 |
| FR2175827B1 (enrdf_load_stackoverflow) | 1976-06-11 |
| FR2175827A1 (enrdf_load_stackoverflow) | 1973-10-26 |
| GB1394947A (en) | 1975-05-21 |
| CH575370A5 (enrdf_load_stackoverflow) | 1976-05-14 |
| US3916009A (en) | 1975-10-28 |
| JPS4911818A (enrdf_load_stackoverflow) | 1974-02-01 |
| SU474970A3 (ru) | 1975-06-25 |
| IT979837B (it) | 1974-09-30 |
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